Pumpkin Whoopie Pies with Chocolate Cream Cheese Filling

I’ve missed this. I’m sitting on a Greyhound bus, long after sundown, and all I can hear is the quiet murmurings of other passengers and the soft clicks as I tap my keys. For the holidays, I’m heading to New York City, and then Pennsylvania, where my uncle and aunt and cousin live. It’s the first time in weeks I’ve had some quiet time to myself, without an assignment or shift or appointment. I’ve missed being able to sit alone with my thoughts and write.

Classes ended this afternoon, and it was unusually quiet on the floor today. Everyone was packing up, unplugging their lamps and emptying their fridges, stopping at every room down the hallway to say goodbye. We’re spreading out from California to Maine, retreating back to where we came from. It’s Thanksgiving break, and even though I’m not flying back to Seattle, it’s got me thinking about home.

I haven’t been in a bus or car in a long time. Back home I used to love, love, love driving alone at night – the way every turn of the car feels smooth and controlled, the open silence on the road, and the glittering pairs of lights in every direction, like cat eyes. Right now, in the dark, it’s easy to imagine I’m in Seattle. I look out the window and realize we’re on I-90, and that if we just kept driving west on this freeway until we hit the opposite coast, I’d be back.

It’s not that I’m homesick, because I’m truly not. There’s a soft spot in my heart for Seattle, but at the same time, home is in people, not places. Home is my mom, drinking jasmine tea on our patio. It’s my dad, who’s flying to Pennsylvania for Thanksgiving. And it’s the people on my floor. I can feel myself falling for the incredible people I’ve met here, and as everyone moves out, I can feel bits of my home scattering across the country. I’m reluctant to leave them, even for a week.

But I see the details of my old life everywhere. It’s begun to rain in Boston, a damp downpour that feels like hot breath on your neck. It makes me think of how green the air smelled and how dark the pavement became in Seattle. Sometimes, in line at Starbucks, I forget where I am. Then I step outside and suddenly realize I’m far away… watching the trees exhale burnt orange and crimson, the kind of seasonal change I always said I wanted to experience.

The other night at the restaurant, I decided to make small talk with one of my tables. They said they were just visiting Boston, and that they’d flown in from – Seattle. We talked a little longer and discovered that we live in the same region. In fact, their daughter goes to my old middle school, is in my gifted program, and is learning from my old teachers. I’d have never known, if they hadn’t sat at this restaurant, at this time, in my section.

I’m excited to spend time with my family, especially since I don’t frequently see my relatives on the east coast. I can’t begin to describe how excited I am to eat some real food. My college has been hosting Thanksgiving themed dinners, and somehow their canned cranberry jelly and paper-dry turkeys don’t do my favorite holiday justice.

And I’m ecstatic about getting some baking done.

Even though I have all my tools and supplies, and even an oven if I walk to another dorm, I haven’t had time to buy ingredients or spend time in a kitchen. It’s strange that people here are getting to know me without baking being a huge factor in my life. Maybe at the end of this weekend, I can bring a box of sweets back to my floor.

I’m thinking whoopie pies. I’ve met plenty of New Englanders here who are dead serious about the whoopie pie. Every time I hear someone get defensive about the dessert’s origin or characteristics, I can’t help but smile.

There aren’t a lot of whoopie pies on the west coast. Plenty of people don’t know what they are – just two soft cake-like cookies with some sort of filling sandwiched in between. While I’ve never had a “real” whoopie pie, I can tell you that these ones taste pretty incredible. Especially after a chill in the fridge, with a tall glass of cool milk, a scattering of crisp leaves at your feet and a friend at your side.

I made these pumpkin whoopie pies with chocolate cream cheese filling before I left for college, and they strike such a great balance of richness and spice. The pumpkin cookies are soft and tender, dense, dark with spices, like autumn in your mouth. As for the chocolate, I just can’t get enough, and the cream cheese filling adds a bittersweet tang to complement the cookie.

If I make these again this week, it’ll probably remind me like crazy of Seattle. I’m not sure yet if that’s a good or bad thing. Whatever the case, it’ll cheer up my floormates, and bring a little bit of one home to another.

Happy Thanksgiving!

The first time I made these, I thought the cookies came out a little too soft and tender, so I baked them another 10 minutes and they were great. I liked sneaking them out of the fridge, eating them chilled with cold milk.

To make the whoopie cookies: Preheat the oven to 350 degrees F and line two half sheets with parchment paper or silpat baking mats.

In a large bowl, whisk together the dry ingredients: the flour, salt, baking powder, baking soda, cinnamon, ginger, and cloves. In another large bowl, whisk together the dark brown sugar and the vegetable oil until well combined. Whisk in the pumpkin puree, then stir in the egg and the vanilla extract. Stir in the dry ingredients until just combined.

Drop the batter by the heaping tablespoon an inch apart on the baking sheets (I used a little ice cream scooper to get evenly sized whoopie pies.) Bake until the cookies just start to crack at the top and a toothpick comes out clean, about 15 minutes (mine took 20-25 minutes.) Let cool completely on the pan.

To make the dark chocolate cream cheese filling: Sift the powdered sugar and cocoa powder into a bowl and set aside. In the bowl of an electric mixer, beat the butter and cream cheese until very smooth and fluffy, about 2 minutes. Beat in the powdered sugar and cocoa powder on low speed until incorporated, then mix in the vanilla extract and milk until smooth.

To assemble the whoopie pies: Spoon some filling into a piping bag fitted with a large round open tip. Pipe a dollop of filling onto the flat side of one whoopie cookie and top with another. Refrigerate cookies until ready to eat and keep in the refrigerator, covered with plastic wrap, for up to three days.

Hi Elissa,
I have followed your blog for awhile and I think it is fantastic. I go to school in Oregon, but am currently studying abroad in Sevilla, Spain. Your posts always make me feel like I have a little slice of home sitting in front of me and you manage to articulate what I miss most about the Pacific North West. This recipe looks incredibly delicious. I will have to remember it for next Thanksgiving!
Happy Baking,
Hannah

I’ve been seeing this recipe everywhere! I’m glad you’re able to spend the holidays with your family and still get a sense of “home” no matter which coast you’re on. These whoopie pies certainly evoke warmth in the cold weather!

Every time you post, I am blown away by how quickly I am drawn into each one of your sentences. Your posts always make me so quiet and reflective, myself. This was a beautiful way to start my Wednesday. Thank you.

(Oh, and the whoopie pies look delicious! I didn’t even know these things existed until I started reading food blogs.)

Enjoy New York Elissa! If you have a chance you must must must visit The Strand on Broadway and East 12th street. It’s 18 miles of books and my favorite place in the entire city. Aside from seeing friends and family, it’s the reason why I’m most excited to be home.

I hope that you have a very happy Thanksgiving and that you get a chance to bake again. These whoopie pies look marvelous. I hope that your floor enjoys them!

Beautiful, nostalgic post. Thanks. This will be the first time that I will celebrate Thanksgiving, though admittedly, I will be celebrating it on Saturday, my family is Irish and here in Ireland, the holiday of Thanksgiving is non-existent, people don’t even know at what time of year it falls, let alone a specific day, so I think I’ll get away with it! My family will all be away in far-flung parts of the world – Paris, Ukraine, Sydney and Kyrgzstan so I will be cooking for fifteen close friends. Hopefully I can make it a tradition.

Elissa, I have been following your blog for some time and felt it was time to show my appreciation. You write extremely well for someone your age, you use words beautifully and it all seems so natural.I like how you give a story to your recipes, unlike many of the other food blogs out there, it gives a great depth to your blog and makes it stand out from the rest. I am in University in the UK and now how you feel when you don’t have time/facilities to bake, but when you do, you have a new appreciation for it! Keep up the great work and I hope you successfully juggle your busy schedule. Happy Thanksgiving.

Once again, a beautiful entry. How awesome that your dad will be flying to Pennsylvania to see you. I wonder who is the most exacted, you or your dad? Have a wonderful time and try to catch up on a little rest, too.
I’ve got to try those Whoopie Pies. Chocolate and Pumpkin-two of my favorites things!

I absolutely love reading your blog. I am a graduate of Emerson and even though it has been many years since I graduated, I will always remember my four years there with tremendous fondness. My closest friends, all these years later, are my Emerson friends. Also, my son went to college outside of Seattle and I fell in love with the city when we visited him You are an amazing young woman and I am grateful that I found out about you in the Emerson alumni magazine…an outstanding article about you!!

My boyfriend’s mom sent basically these exact same things to us (just not chocolate) earlier this semester! And, being from Seattle, I was like, what are these? But they’re so delicious! I’ll have to try your recipe and see how it compares. :)

Happy Thanksgiving, Elissa! Wish you were here – you would have loved Will Bake for Food! Hope to see you at Christmas to hear all about your new jobs and school. Glad you’re able to get a little time to yourself this week. Enjoy it, and good luck with finals.

“Maybe at the end of this weekend, I can bring a box of sweets back to my floor.”
I think this is an excellent idea. Were I someone who lives on your floor, I would greatly enjoy that idea. If I lived there. I think your floormates would appreciate coming back to Elissa-baked food in the common room, even if that hypothetical common room smelled terrible. But, again, I don’t know anything about that.

These look fantastic, especially with chocolate! I’ve made some with a maple cream cheese filling but had not thought of chocolate! I am now excited to try it this way. I hope you are having a wonderful Thanksgiving and baking away in your relatives’ kitchen. :)

Your comments about people getting defensive about the origin of the whoopie pie made me giggle; the first time I truly had one (being a west coaster myself, I live in Spokane) was when I visited PA for the first time (my husband is originally from there). And you are very correct. There are different brands and people are VERY protective of which brand got it “right”. I look forward to making these and enjoy your holiday with friends and family!

I’ve been reading your blog for quite awhile now and it’s always amazing. :) This recipe sounds pretty great. I recently did a pumpkin bundt cake with cream cheese buttercream, and that was pretty awesome too. Haven’t gotten around to blogging about it yet though.

You pretty much inspired me to start my own blog. It would be amazing if you’d check it out.

I made these today!!! They are so yummy! I love the recepie beacause they not only make your kitchen smell amazing but it’s a prefect recepie for chilly weather : )
I had a bit of an accident with the filling because I wrote ONE cup of cocoa powder on my flashcard and it was only HALF of a cup xp
THANKFULLY I was adding it little by little so I realized one cup was waay to much. Another mistake I made was adding the cocoa powder lastly so it in a way coated the cream cheese…I had to litterally use my hands to blend in the cocoa powder and cream cheese..it worked thou : ) So next time i make them I’ll be sure to mix the cocoa powder AND powdered sugar so I can add them together. I made my cookies a little bigger so I only got six out of my batter (and a mini one). The filling was almost the exact ammount I needed. Thanks soo much (: I highly recommend these!!

There’s four ounces of cream cheese sitting in my fridge that’s asking to be used up like this. I don’t really understand what’s the deal with whoopie pies (admittedly the only ones I’ve had are a bit…lacking), but this seems as good a place as any to start.

Glad to hear you have the option to bake still, and that you still had Thanksgiving on the east coast. Only a few more weeks til winter break comes along. Cheers til then. :)

I love reading your blog. Everything about it is so peaceful. I am in college now, and I miss baking so terribly that the first thing I do when I get home is make sure I bake something for the family. I have never had a whoopie pie, but these look scrumptious. :)
Now you can cross them off your goals list too.

Just had to comment finally. :)
Been reading your blog for awhile and I just have to say that your recipes look delicious and your writing is so eloquent. I think you will make a wonderful journalist. Wishing you the best. Happy Holidays!!

I am going to be going off to college this coming up year, and I feel like I will be homesick, because I am very close with my family. Your blog showed me that not only will my home be with my family, but with my friends that I will meet at school and this has made even more excited to go off on my own!

When you say that “home is in people, and not in places” I cannot help but feel as though these words are taken straight from my mouth. I could not agree with you more, and I believe there to be a true beauty in this statement. Home is not in the walls of the house that you grew up in (it may be to some standard, but not completely), it is in your mothers home cooked meals, your fathers ridiculous jokes, and your siblings’ snotty remarks. Home is conversation, it is laughter, it is passion, and it is being with the ones you love regardless of the location. If the love of your family surrounds you, you are home, and what could be better than that?

These look absolutely DELICIOUS ! I live in Australia so we cannot buy canned pumpkin here and I love that you haven’t used canned products in your recipe – real, from scratch, created recipes – have to make these, I am DROOLING ! hehe